FI90660B - Indenderivat och förfaranden för deras framställning - Google Patents

Indenderivat och förfaranden för deras framställning Download PDF

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Publication number
FI90660B
FI90660B FI875050A FI875050A FI90660B FI 90660 B FI90660 B FI 90660B FI 875050 A FI875050 A FI 875050A FI 875050 A FI875050 A FI 875050A FI 90660 B FI90660 B FI 90660B
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FI
Finland
Prior art keywords
formula
indene
trifluoromethyl
cyano
compound
Prior art date
Application number
FI875050A
Other languages
English (en)
Finnish (fi)
Other versions
FI90660C (sv
FI875050A0 (sv
FI875050A (sv
Inventor
Klaus Peter Boegesoe
Michael Bech Sommer
Original Assignee
Lundbeck & Co As H
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Publication date
Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H
Publication of FI875050A0 publication Critical patent/FI875050A0/sv
Publication of FI875050A publication Critical patent/FI875050A/sv
Publication of FI90660B publication Critical patent/FI90660B/sv
Application granted granted Critical
Publication of FI90660C publication Critical patent/FI90660C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/38—Unsaturated compounds containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Iron Core Of Rotating Electric Machines (AREA)
  • Two-Way Televisions, Distribution Of Moving Picture Or The Like (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Automatic Cycles, And Cycles In General (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Catalysts (AREA)
  • Indole Compounds (AREA)

Claims (15)

1. Indenderivat, kännetecknat därav, att det har formeln I 5 (R >η-^Πί»3
10 R1 CN där R1 är a) en fenylgrupp, som kan vara substituerad med en eller flera halogener, lägre-alkyl-, lägre-alkoxi-, läg- 15 re-alkyltio-, acetylamino-, metylendioxi- eller trifluor-metylgrupper, b) en naftylgrupp, c) en tiofen-, pyridin- eller pyrrolgrupp, som kan vara substituerad med en eller flera lägre alkylgrupper,
20 R2 är H, halogen, lägre alkyl, lägre-alkyltio, lägre-alkylsulfonyl, di-lägre-alkylsulfamoyl, cyano, tri-fluormetyl, lägre alkoxi eller nitro, R3 är CN, C00R4, -CON(R4)2 eller COR4, där R4 är en lägre alkylgrupp, ooh n är ett heltal 1-3.
2. Indenderivat enligt patentkravet 1, kanne- t e c k n a t därav, att R1 är en fenylgrupp, som kan vara mono- eller disubstituerad med klor, fluor, metyl, metoxi, acetylamino eller trifluormetyl; en pyrrolgrupp, som kan vara substituerad med metyl; en tiofenring, som 30 kan vara substituerad med metyl; en pyridinring, som kan vara substituerad med metyl; eller en naftalenring; R2 är väte, klor, brom, fluor, metyl, metoxi eller trifluormetyl; R3 är -COOCH3, -CN eller -C0N(CH3), och n är 1.
3. Indenderivat enligt patentkravet 1 eller 2, kännetecknat därav, att R1 är en fenylgrupp. 21 9 Γ 6 6 O sotn kan vara substituerad med klor, fluor eller trifluor-metyl; R2 är väte, klor, fluor, metyl, metoxi eller tri-fluormetyl i 6-ställning; R3 är -COOCH3, -CN eller -CON(CH3)2 och n är 1,
4. Indenderivat enligt patentkravet 1 eller 2, kännetecknat därav, att R1 är en tiofenring, som kan vara substituerad med metyl; R2 är väte, klor, fluor, metyl, metoxi eller trifluormetyl i 6-ställning; R3 är -COOCH3, -CN eller -CON(CH3)2 och n är 1.
5. Indenderivat enligt patentkravet 1, känne tecknat därav, att det är l-amino-3-cyano-3-(3,4-diklorfenyl)-l-inden-2-karboxylsyra-metylester.
6. Indenderivat enligt patentkravet 1, kännetecknat därav, att det är l-amino-3-cyano-3-(4- 15 fluorfenyl)-6-klor-l-inden-2-karboxylsyra-metylester.
7. Indenderivat enligt patentkravet 1, kännetecknat därav, att det är l-amino-3-cyano-3-(4- fluorfenyl)-l-inden-2-karboxylsyra-metylester.
8. Indenderivat enligt patentkravet 1, k ä n n e - 20 tecknat därav, att det är l-amino-3-cyano-3-(tie- nyl-3)-6-klor-l-inden-2-karboxylsyra-metylester.
9. Indenderivat enligt patentkravet 1, kännetecknat därav, att det är l-amino-3-cyano-3-(tie-nyl-3)-l-inden-2-karboxylsyra-metylester. 25 10. Förfarande för framställning av ett indenderi vat enligt patentkravet 1, kännetecknat därav, att a) en 2-halogenbensonitril med formeln 35 där R2 och n betecknar sanuna som ovan och X är halogen. 22 9 Π 6 60 omsätts med en förening med formeln I^CHjCN, där R1 be-tecknar samma sora ovan, varvid erhälls en förening med formeln
5 CN ii CH CN il 10 som kan antingen 1. isoleras och vidare omsättas i ett organiskt lösningsmedel med en förening med formeln YCH2R3, där Y är Cl, Br eller I och R3 betecknar samma som ovan, eller 2. vidare omsättas in situ med en förening med 15 formeln YCH2R3, eller b) en 2-halogenbensonitril med formeln V omsätts med en förening med formeln R^HCN-CHjR3, där R1 och R3 betecknar samma som ovan; varefter den erhällna föreningen med formeln I isoleras. 20 11. Förfarande enligt patentkravet 10, känne- t e c k n a t därav, att R1, R2, R3 och n betecknar samma som i patentkravet 2.
12. Förfarande enligt patentkravet 10, känne-t e c k n a t därav, att R1, R2, R3 och n betecknar samma 25 som i patentkravet 3.
13. Förfarande för framställning av föreningar med formeln 30 (fi2)n--O IV R1 där R1, R2 och n betecknar samma som ovan, känne-35 tecknat därav, att en förening med formeln 23 9 Γ 6 60 -Ν Η_ R CN där R1, R2, R3 och n betecknar samma som ovan, upphettas under hydrolytiska betingelser, eventuellt under oxidati-10 va betingelser, och en förening med formeln
15 COOH R1 isoleras och föreningen med formeln III upphettas i ett basiskt organiskt lösningsmedel, varefter indanderivatet 20 med formeln IV isoleras.
FI875050A 1986-12-01 1987-11-16 Indenderivat och förfaranden för deras framställning FI90660C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8628644 1986-12-01
GB868628644A GB8628644D0 (en) 1986-12-01 1986-12-01 Intermediates

Publications (4)

Publication Number Publication Date
FI875050A0 FI875050A0 (sv) 1987-11-16
FI875050A FI875050A (sv) 1988-06-02
FI90660B true FI90660B (sv) 1993-11-30
FI90660C FI90660C (sv) 1994-03-10

Family

ID=10608224

Family Applications (1)

Application Number Title Priority Date Filing Date
FI875050A FI90660C (sv) 1986-12-01 1987-11-16 Indenderivat och förfaranden för deras framställning

Country Status (17)

Country Link
US (1) US4873344A (sv)
EP (1) EP0271225B1 (sv)
JP (1) JP2622135B2 (sv)
AT (1) ATE95810T1 (sv)
AU (1) AU609751B2 (sv)
CA (1) CA1302420C (sv)
DE (1) DE3787790T2 (sv)
DK (1) DK626587A (sv)
ES (1) ES2059396T3 (sv)
FI (1) FI90660C (sv)
GB (1) GB8628644D0 (sv)
IE (1) IE60380B1 (sv)
IL (1) IL84429A (sv)
NO (1) NO175527C (sv)
NZ (1) NZ222614A (sv)
PT (1) PT86242B (sv)
ZA (1) ZA878993B (sv)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5643784A (en) * 1990-12-04 1997-07-01 H, Lundbeck A/S Indan derivatives
NZ243065A (en) * 1991-06-13 1995-07-26 Lundbeck & Co As H Piperidine derivatives and pharmaceutical compositions
DK55192D0 (da) * 1992-04-28 1992-04-28 Lundbeck & Co As H 1-piperazino-1,2-dihydroindenderivater
DK78692D0 (da) * 1992-06-12 1992-06-12 Lundbeck & Co As H Dimere piperidin- og piperazinderivater
EP1458704A1 (en) * 2001-12-21 2004-09-22 H. Lundbeck A/S Aminoindane derivatives as serotonin and norepinephrine uptake inhibitors
IS7282A (is) * 2001-12-21 2004-05-21 H. Lundbeck A/S Amínóindan afleiður sem serótónín og noradrenalínupptökuhindrar
US8217041B2 (en) 2005-11-08 2012-07-10 Laboratories del Sr. Esteve, S.A. Indene derivatives, their preparation and use as medicaments
TW200819426A (en) 2006-08-31 2008-05-01 Lundbeck & Co As H Novel indane compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1124682A (en) * 1966-06-21 1968-08-21 Wyeth John & Brother Ltd Preparation of amines
DE1793488A1 (de) * 1968-09-25 1972-02-24 Knoll Ag Aminobenzocycloalkylnitrile
IE50867B1 (en) * 1980-02-29 1986-08-06 Kefalas As Indane derivatives
IL66831A0 (en) * 1981-10-05 1982-12-31 Kefalas As Indane derivatives
IE55972B1 (en) * 1982-10-07 1991-03-13 Kefalas As Phenylindene derivatives,acid addition salts thereof,and methods of preparation

Also Published As

Publication number Publication date
DK626587D0 (da) 1987-11-30
GB8628644D0 (en) 1987-01-07
FI90660C (sv) 1994-03-10
US4873344A (en) 1989-10-10
DE3787790D1 (de) 1993-11-18
IL84429A0 (en) 1988-04-29
NO175527B (no) 1994-07-18
PT86242B (pt) 1990-11-07
DK626587A (da) 1988-06-02
FI875050A0 (sv) 1987-11-16
IE60380B1 (en) 1994-07-13
EP0271225B1 (en) 1993-10-13
EP0271225A2 (en) 1988-06-15
NO874990D0 (no) 1987-11-30
JP2622135B2 (ja) 1997-06-18
ATE95810T1 (de) 1993-10-15
NO874990L (no) 1988-06-02
AU8192887A (en) 1988-06-02
FI875050A (sv) 1988-06-02
JPS63154652A (ja) 1988-06-27
IE873019L (en) 1988-06-01
IL84429A (en) 1993-05-13
ZA878993B (en) 1988-10-26
ES2059396T3 (es) 1994-11-16
PT86242A (en) 1987-12-01
CA1302420C (en) 1992-06-02
NZ222614A (en) 1990-08-28
NO175527C (no) 1994-10-26
DE3787790T2 (de) 1994-04-14
EP0271225A3 (en) 1989-12-06
AU609751B2 (en) 1991-05-09

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Owner name: H. LUNDBECK A/S